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Movies Like The Worst Day of My Life in Detroit

If you liked The Worst Day of My Life in Detroit (2023), a comedy and romance movie directed by Jack Henry Calverley, here are 20 movies with a similar feel, based on TMDB's recommendations. Each one links to its cast, trailer and where it's streaming.

  1. 1Balls Up

    Balls Up (2026)

    ★ 5.8/10Also comedy and adventure

    Two marketing executives go "balls out" and pitch a bold full‑coverage condom sponsorship with the World Cup. After their drunken celebration in Brazil sparks a global scandal, they must outrun furious fans, criminals…

  2. 2Fairy Tales

    Fairy Tales (1978)

    ★ 6/10Also adventure and comedy

    On his twenty-first birthday, the Prince goes on a quest that takes him across the land searching for the one woman that gets him sexually excited, Princess Sleeping Beauty.

  3. 3The Right Kind of Wrong

    The Right Kind of Wrong (2013)

    ★ 5.9/10Also romance and comedy

    A stubborn idealist spies a bride on her way to her wedding and immediately falls in love with her.

  4. 4The Incredible Jessica James

    The Incredible Jessica James (2017)

    ★ 6.1/10Also romance and comedy

    Burned by a bad breakup, a struggling New York City playwright makes an unlikely connection with a divorced app designer she meets on a blind date.

  5. 5Girl on a Bicycle

    Girl on a Bicycle (2013)

    ★ 5.9/10Also comedy and romance

    Paolo, an Italian tour bus driver living in Paris, has just summoned up the courage to propose marriage to his German girlfriend Greta. However, a chance encounter with a French woman on a bicycle the very next day…

  6. 6French Girl

    French Girl (2024)

    ★ 6.2/10Also romance and comedy

    Sweet Gordon, an affable English teacher in Brooklyn, has beaten the odds; a French Girl has fallen in love with him and he’s fallen even harder back. But their future is thrown into limbo when she interviews for an…

  7. 7Sex Appeal

    Sex Appeal (2022)

    ★ 6.6/10Also comedy and romance

    Avery, a teenager with a tendency towards perfectionism, enlists her friend Larson to help her prepare for her first time with her long-distance boyfriend.

  8. 8Mr. Right

    Mr. Right (2016)

    ★ 6.4/10Also comedy and romance

    A girl falls for the "perfect" guy, who happens to have a very fatal flaw: he's a hitman on the run from the crime cartels who employ him.

  9. 9¿Quieres ser mi hijo?

    ¿Quieres ser mi hijo? (2023)

    ★ 8.4/10Also comedy and romance

    Lu, a conformist woman in her forties, learns that her 15-year partner has been having extramarital affairs. Starting from scratch, she gets involved in an unexpected relationship with a young womanizer.

  10. 10Maintenance Required

    Maintenance Required (2025)

    ★ 6.1/10Also romance and comedy

    Charlie, the fiercely independent owner of an all-female mechanic shop, is forced to reevaluate her future when a flashy corporate competitor moves in across the street. Seeking comfort, she turns to an anonymous…

  11. 11A Nice Girl Like You

    A Nice Girl Like You (2020)

    ★ 5.8/10Also comedy and romance

    Lucy Neal is thrown for a loop when she is accused of being too inhibited by her ex-boyfriend. In an effort to prove him wrong, Lucy creates a rather wild to-do list that sends her on a whirlwind and surprising journey…

  12. 12Meet Cute

    Meet Cute (2022)

    ★ 5.8/10Also comedy and romance

    A wildly inventive deconstruction of the romantic comedy built around the question: What would you do if you could travel to your loved ones’ past, heal their traumas, fix their problems, and change them into the…

  13. 13The List

    The List (2023)

    ★ 5.9/10Also romance and comedy

    After her fiance sleeps with a celebrity on his free pass list, Abby Meyers, with nothing but five names and a fantasy shared by millions, sets out for Los Angeles to sleep with someone from hers.

  14. 14I Want You Back

    I Want You Back (2022)

    ★ 6.3/10Also comedy and romance

    Peter and Emma thought they were on the precipice of life’s biggest moments – marriage, kids, and houses in the suburbs – until their respective partners dumped them. Horrified to learn that the loves of their lives…

  15. 15My Favorite Brunette

    My Favorite Brunette (1947)

    ★ 6.6/10Also comedy and romance

    Ronnie Jackson is a lowly baby photographer who secretly fantasizes about being a private detective. When a lovely baroness actually mistakes him for one and asks him to help locate her missing husband, Baron Montay…

  16. 16Players

    Players (2024)

    ★ 6.1/10Also romance and comedy

    New York sportswriter Mack has spent years devising successful hook-up "plays" with her friends, but when she unexpectedly falls for one of her targets, she must learn what it takes to go from simply scoring to playing…

  17. 17Sheroes

    Sheroes (2023)

    ★ 5.8/10Also comedy and adventure

    When four thick-as-thieves friends arrive in Thailand, they quickly find themselves in over their heads. Fighting to stay alive, they employ their unique set of skills and unleash their fierce loyalty in a…

  18. 18Long Weekend

    Long Weekend (2021)

    ★ 6.8/10Also romance and comedy

    Bart's chance encounter with the enigmatic Vienna leads to a whirlwind weekend together. The two fall fast and hard, but both carry secrets that could be their undoing or the chance for a fresh start.

  19. 19Desperados

    Desperados (2020)

    ★ 6/10Also comedy and romance

    A panicked young woman and her two best friends fly to Mexico to delete a ranting email she sent to her new boyfriend. On arrival, they run into her former beau, who soon gets caught up in their frantic scheme.

  20. 20My Sassy Girl

    My Sassy Girl (2008)

    ★ 6.8/10Also comedy and romance

    A guy has his life planned out until he is wooed, groomed and then dumped by an elusive woman.

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